Several reports have said that even since that trade, the Raiders owner Mark Davis has remained close with Gruden. According to The MMQB's Albert Breer, Davis and the Raiders would consult Gruden on decisions like draft picks.

That role as an unofficial adviser may have planted the seeds for the reunion.

According to Breer, Gruden was a big fan of Derek Carr coming out of college and that admiration convinced Davis that the Raiders should take him with the fourth pick in the 2014 draft. The Raiders instead took Kahlil Mack at four, but were able to draft Carr in the second round. Breer reported that some believe the Raiders felt getting Carr was a way to potentially reunite with Gruden.

From Breer:

"Oakland owner Mark Davis has been known to consult with Gruden on football matters, and Gruden made clear to Davis how much he thought of Carr, to the point where Davis wound up advocating to GM Reggie McKenzie that the team take Carr with the fourth overall pick. McKenzie and the staff wound up holding off the dogs on that one, and the rest actually played out perfectly. The team got a generational talent at 4, in Khalil Mack, and still wound up with Carr in the second round. But to the coaches who were there, there was a feeling that Davis, who'd always been interested in bringing back Gruden, wanted Carr badly because he knew that Carr, if he panned out, could wind up being a chip to entice the old coach."

Certainly anyone who has watched a "Monday Night Football" broadcast with the Raiders and Gruden recognized that Gruden is a fan of Carr, one of the young star quarterbacks in the league. However, a look back at Gruden's "QB Camp" segment on ESPN with Carr in 2014 also showed what a fan he was of Carr coming out of Fresno State.

During the segment, when Gruden asked Carr whether he would draft himself or his older brother, David, a former NFL quarterback, Gruden interrupted and said, "I want you. What do you say about that?"